The Pain and Suffering of Dean Winchester
by Sara Jessica Grissom
Summary: What can Hell do to you? How long would it take demons in Hell to break you down?. Chapter 3 up. Please R&R. Thank you.
1. Welcome to Hell

**Disclaimer: I own NOTHING. All characters and such belong to the respective owners. Also the the quote, "you can stick where the sunshines"comes from one of the episodes and does not belong to me. **

**A/N: I do not have a beta for this story so all mistakes are mine. Please remember that this is not light and fluffy as it is Dean in Hell. **

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Today is a new day. Not that it means anything. Not like today will be any different from yesterday. There will be pain and suffering. I'll be ripped to shreds and at the end of the day then HE will ask me the same question he did the day before. Should it be any surprise then that my answer will be the same as usual?

Day after day, month after month, and year after year I endure this physical and mental torture. The mental is self-inflicted. But the physical is not. The demon, the son of a bitch demon that does this to me every single day goes by the name of Alistair. I watch him smile and laugh as he slowly draws blood with his dagger, as he rips my flesh from my bones. The asshole gives me this big shit-eating grin and then pulls the nails on my fingers clean away. I can't help but scream. This time I yell no words or expletives at Alistair just a scream of pain.

The mental torture is worse because all I can think when I am not screaming is that I've left Sammy all alone. I know there was nothing for it. I had to give up my soul for his life. There was just nothing else that could've been done. Still, it torments me. And I can never ever escape it anymore than I can escape the physical torture. I can tell the day is coming to an end. Alistair approaches me, looks me square in the face and asks,

"Would you like off the rack? All you have to do say yes. You can end the pain. Help me torture other souls that enter Hell?"

I look at him full on and spit in his face and then I say it, "You can stick it where the sun shines, you son of a bitch."

"Now, now Dean that's no way to talk," he says smoothly, tauntingly.

I glare at him, "You think I care whether or not you think what I say is a good way to talk."

He smiles at me and walks away. Alistair will be back it's all a matter of time. In his absence, images of Sam come back to me. Images of him dying, of him coming back to life, and the look on his face when he found out I traded my soul for his life. These moments happened a lifetime ago or so it seems. All of a sudden I feel a toenail being removed but I manage to keep my mouth shut just this once. So a new day has started. How I wish that it would not be the same as yesterday, but it will. It's always the same. I cannot allow it to be different because if I do it'll mean I am torturing someone's soul. As he rips another toenail from my toes he speaks to me in a deadly quiet though amused tone,

"You know this is just so much fun. What do you think Dean? Couldn't doing this to a soul be loads of fun?"

I yell at him, "Fuck you, Alistair, you sick bastard." Some days he does this when he's torturing me. He'll talk to me ask me questions. It is the only thing that changes. His comments aren't quite the same as the ones before. Other days he makes no comments at all. Alistair just laughs and smiles and mouths things to himself on those days.

He moves onto my other foot to pry toenails off and again he talks to me in a laughing tone,

"Today isn't just a new day Dean it's a new month, a new year. What do ya know, it's your twenty ninth year on the rack."

I say nothing to this. There isn't anything to say. Instead I give an earsplitting scream as he slowly starts to cut my toes off. He just smiles at me with that look in his eye. The look that tells me he's enjoying every minute of this, and its telling me that he will get his way eventually. He thinks that someday, some year I'll finally take his deal to get off the rack.

The truth is some days I really consider it. I have come so close many days to telling Alistair I will do it; that I'll torture souls with him. But I never say it because to do that would make me a monster. I may not have big scary claws or scary teeth but nonetheless I would be a monster because I would be doing what he does to me. All the same I still think about how nice it would be to not have my toes, fingers, and flesh ripped from me. He catches my attention again and moves from feet to my leg and starts stripping away flesh. As I scream I think about Sammy for the billionth time. I know he's probably doing all right without me but even here in Hell I worry about him.

For a year I endlessly suffer through Alistair's torture and giving him the same answer every day to his question. But today marks my thirtieth year down here and today I can take it NO MORE. He approaches me and would like to know,

"Would you like off the rack? All you have to do is say yes. You can end the pain. Help me torture other souls that enter Hell?"

Glaring at him with tears in my eyes I whisper, "Get me off the rack. I will take your deal."

At this Alistair gives me his big shit- eating grin. He undoes my bonds and I slowly get down from the rack. Finally free of the physical torture. This doesn't stop the mental onslaught from the part of me that knows I shouldn't have taken the deal. I shut it up though told myself there wasn't any other way. I lied to myself. Then Alistair spoke again in a slithery tone,

"Today is a new day my apprentice. Come let me teach you the ways of torture."

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**Please read and review. I would really like to know what you think. Besides you know you want to and I'll give you a cookie. :P. **


	2. Carving, Oh Wonderful Carving

**Disclaimer: Once again I own Nothing. **

**Note: Still no beta all mistakes belong to me. **

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I stand there watching Alistair strip the flesh off someone else as he talks to me. He tells me the best ways to slowly torment someone. Just when I think he's going to finish off the guy for the day he turns to me. With a small smirk he says,

"It's your turn now, Dean. Show me what you got."

Staring at Alistair I walk to the rack, and pick up the dagger. I draw blood with my first cut along with a horrific scream from the man. I cut some more and more and more. Every slice, every scream made me feel better. Better that I wasn't the one on the rack that I didn't have to withstand the pain, the hurt. And yet there was still some small, very small part of me wondering how the hell I could be doing what I am doing. But I ignore it and continue on until the man is completely destroyed.

Turning back to Alistair I level a look at him. Upon seeing me he laughs like it was just the funniest fucking thing he's ever seen. I walk past him in silence wishing he would shut that mouth of his. I don't know how far away I get from him before he addresses me finally,

"That was very good for your first time. You definitely need a lot more work though."

I keep going. No need to stop. No need to answer him. He isn't looking for a response and I don't have one for him.

As months and years go by I learn more. I am methodical and exacting. Not perfect not yet. I still have a lot to learn. A lot of people think they know what it's like to be beyond the point of caring what they're doing or what's happening so long as it brings them relief. They have no idea what it is to NOT care. Nor can anyone understand what it's truly like. That is unless you are in Hell. I don't care…about the souls I torture, and tear apart. It matters not to me how much another suffers because it means I am not. Not only that but I am starting to enjoy pulling flesh from bone, nail from finger. Bringing pain to someone else means I don't have to pay attention to my pain. I no longer think about Sammy as often as I did before. Everything that used to mean something to me when I was on earth is fading away.

I pulled out the knife. I leaned down and whispered, "You're gonna wish you never existed." Then slowly and carefully I started digging into the man's skin with the tip of the blade. The blood pours out. He screams and I continue on. Carving and ripping, ripping and carving all day long. Briefly I stop, the man cries out, "Please…please stop." I just look at him and go back to business with a small satisfied smile on my face. Bringing the point of the knife to his neck I slice slowly across the skin and he howls. Again and again I cut. The day is ending, I move towards the guy's balls and dick with knife. As I tear into the soft skin a joy fills me. It's the kind of joy that a kid has when he plays with a new toy. Upon finishing my torture of the man I hear a deep manic type of laughing. At first I am sure it's coming from Alastair and then I realize it's me.

The day finally ends.

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**_I am not sure if there will be a third chapter or not. And I have yet to receive reviews. You know you want to review. There are gummy bears to be received for doing so :D. _**


	3. It's Been a Pleasure or Not

**Disclaimer: _The part after he is out of the coffin belongs to Supernatural_** _**Episode Lazarus Rising. So as usual I own NOTHING. I only wanted to show Dean's thoughts once he was out of Hell.**_

**Note:** All mistakes spelling, grammar or otherwise is mine as I didn't have a Beta. Oh yes this is the last chapter of the story. It is only because my goal was mostly to tell Dean's story while in Hell and right after he got out and also because well it's where the tv show picks back up obviously.

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Humanity has left me. It's been ten years ago today that I started torturing souls. I am not sure why I didn't accept Alastair's offer in the beginning. I mean after all the past ten years have been a pleasure. The bitch in front of me screams bringing my attention to her. I haven't even started yet.

"I would save your screaming voice, sweetheart," I tell her in a deadly whisper. Picking up Alastair's razor I walk over to her breasts and cut a little line just below the nipple. Tears trickle down her face as she whimpers. I give her a small smile and continue to slice. Finally, the last of her is carved. The day is ending and I turn away closing my eyes. Surprisingly, I feel a sliver of sadness at what I just did. I am not sure why. It's been a long time since I have felt anything other than satisfaction.

Opening my eyes I see a blur running towards me. Completely confused I start to ask what is going on. I never finish my sentence as I am gripped tight near my shoulder.

*_In his coffin in Illinois*_

I awaken in the dark. I am completely alone and not sure what has happened. But within a few seconds I realize I am buried underground in a wood coffin. Panicking I break out. A couple of minutes later I see the sun shining and climb my way out of my coffin. As I turn in a circle all I can think is 'what the Hell?' After some minutes it sets in that I am actually out of Hell. I don't know why or how I got out; I just am out.

Eventually, I make my way out of the woods and to the road. I shouldn't be alive but I am. All of those people I tortured I I…have to find a place to get food and water. I try to shut out the resounding voices in my head. As I walk it is all I hear; the souls screaming and crying, begging and pleading for me to stop. I didn't quit though. I still tore, cut and hurt souls. Never can I change it but for the rest of my life I must save as many people as possible.

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**Reviews are always welcome and I very much enjoy reading them. Let me know what you think. **


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